Light-driven radical copper-catalyzed allylic amination via allylic copper intermediates

Hang Luo, Yupeng Yang, Yunpeng Ma, Fangnian Yu, Min Gao (), Shizhao Xu, Huawei Ju, Yang Li, Kaifeng Wu () and Luqing Lin ()
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Hang Luo: Dalian University of Technology, Central Hospital of Dalian University of Technology, School of Chemistry
Yupeng Yang: Chinese Academy of Sciences, State Key Laboratory of Chemical Reaction Dynamics and Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), Dalian Institute of Chemical Physics
Yunpeng Ma: Dalian University of Technology, Central Hospital of Dalian University of Technology, School of Chemistry
Fangnian Yu: Dalian University of Technology, Central Hospital of Dalian University of Technology, School of Chemistry
Min Gao: Hokkaido University, Institute for Chemical Reaction Design and Discovery (ICReDD)
Shizhao Xu: Dalian University of Technology, Central Hospital of Dalian University of Technology, School of Chemistry
Huawei Ju: Dalian University of Technology, State Key Laboratory of Fine Chemicals
Yang Li: Dalian University of Technology, State Key Laboratory of Fine Chemicals
Kaifeng Wu: Chinese Academy of Sciences, State Key Laboratory of Chemical Reaction Dynamics and Collaborative Innovation Center of Chemistry for Energy Materials (iChEM), Dalian Institute of Chemical Physics
Luqing Lin: Dalian University of Technology, Central Hospital of Dalian University of Technology, School of Chemistry

Nature Communications, 2025, vol. 16, issue 1, 1-11

Abstract: Abstract The synthesis of allylic amines through an outer-sphere nucleophilic substitution mechanism involving electrophilic allyl copper(III) complexes with soft amines represents an uncharted territory in catalysis. This study introduces a radical-based approach for the generation of allylic copper(III) complexes, enabling the efficient synthesis of allylic amines in the presence of alkyl/aryl amines. Through copper photocatalysis, we demonstrate a radical-induced small-ring opening process that produces allylic amines featuring skipped double bonds, while simultaneously achieving highly regioselective 1,4-carboamination of 1,3-dienes with high E/Z selectivity. Mechanism studies substantiate the radical-mediated formation of allylic copper complexes and provide evidence for the involvement of outer-sphere nucleophilic substitution at allylic copper(III) complexes.

Date: 2025
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DOI: 10.1038/s41467-025-64951-5

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